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萝卜硫素在溶剂中的稳定性及降解机制

The stability and degradation mechanism of sulforaphene in solvents.

作者信息

Tian Guifang, Tang Pingwah, Xie Rui, Cheng Li, Yuan Qipeng, Hu Jing

机构信息

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, PR China.

State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing 100029, PR China.

出版信息

Food Chem. 2016 May 15;199:301-6. doi: 10.1016/j.foodchem.2015.12.018. Epub 2015 Dec 8.

DOI:10.1016/j.foodchem.2015.12.018
PMID:26775975
Abstract

Sulforaphene, a natural compound, has been investigated as a potential anticancer agent. However, the stability of sulforaphene, in various solvents, and its degradation pathway have not been appropriately reported. This instability impairs the preparation process, the biological evaluation experiments, and the applications of sulforaphene. In this study, the stability of sulforaphene stored at 26°C was investigated in each of the following six solvents: two kinds of protic solvents (methanol and ethanol) and four kinds of aprotic solvents (acetonitrile, dichloromethane, ethyl acetate and acetone). Sulforaphene was found to be stable in aprotic solvents and unstable in the protic solvents. The degradation products of sulforaphene in protic solvents (methanol and ethanol) were purified by the preparative HPLC and identified by ESI/MS and NMR ((1)H NMR). The degradation pathways of sulforaphene in methanol and ethanol were proposed. It was found that sulforaphene was degraded into two kinds of structural isomer in alcohols.

摘要

萝卜硫素是一种天然化合物,已被作为一种潜在的抗癌剂进行研究。然而,萝卜硫素在各种溶剂中的稳定性及其降解途径尚未得到恰当报道。这种不稳定性影响了萝卜硫素的制备过程、生物学评价实验及其应用。在本研究中,研究了萝卜硫素在26°C下分别在以下六种溶剂中的稳定性:两种质子溶剂(甲醇和乙醇)和四种非质子溶剂(乙腈、二氯甲烷、乙酸乙酯和丙酮)。发现萝卜硫素在非质子溶剂中稳定,而在质子溶剂中不稳定。通过制备型高效液相色谱法纯化了萝卜硫素在质子溶剂(甲醇和乙醇)中的降解产物,并通过电喷雾电离质谱法和核磁共振氢谱对其进行了鉴定。提出了萝卜硫素在甲醇和乙醇中的降解途径。结果发现,萝卜硫素在醇类中降解为两种结构异构体。

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